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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Ashland holiday homes

A two-story building with large windows and a storefront.

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (64 reviews)
"Overall great experience. Very central location. Host lives in building, so is always available. They grow tomato's and cucumbers on the balcony that they invited us to "take as much as you want" My only discomfort with this place was the dust and dirty dishes. The people before us half-washed the things they used and the place seemed like it needed a pass with a vacuum cleaner. The floors were not very clean. In general, I greatly enjoyed my stay here."
United States
David
The price is NZ$407
includes taxes & fees
11 Oct - 12 Oct
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

2. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is NZ$856
includes taxes & fees
3 Nov - 4 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A wooden interior with a central fireplace, benches, and a window offering a forest view.

3. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
The price is NZ$1,196
includes taxes & fees
2 Nov - 3 Nov
Mountain house with Scandinavian BBQ hut and Hot tub
A bedroom with a bed, wooden dresser, ceiling fan, framed pictures, and a view into the kitchen.

4. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is NZ$1,112
includes taxes & fees
14 Oct - 15 Oct
Catskills Escape w/ Hot Tub & Fireplace
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

5. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is NZ$939
includes taxes & fees
3 Nov - 4 Nov
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

6. Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
The price is NZ$788
includes taxes & fees
2 Nov - 3 Nov
Midnight Fox
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

7. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is NZ$735
includes taxes & fees
18 Oct - 19 Oct
West Kill Barnhouse: Ski, Work & Unwind
A house with a fire pit and outdoor seating.

8. The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Hensonville
10.0 out of 10, Exceptional, (8 reviews)
"House had everything, very clean, host very responsive, located close to everything. Great family vacation!"
United States
Jaylyn B.
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

9. Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Interior

10. Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!

Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!
West Kill
10.0 out of 10, Exceptional, (2 reviews)
"If you've lived in an old house before, then you know what to expect. It was good for our needs during our short stay. The house is spacious and there is lots of light. The beds were comfortable and the water pressure was awesome. There is an a/c in every upstairs bedroom."
United States
Alexandra I.
The price is NZ$966
includes taxes & fees
13 Oct - 14 Oct
Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.

11. Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
10.0 out of 10, Exceptional, (1 review)
"Host had an amazing response time. Very easy to talk with via email. She had very clear and easy instructions on check in and check out. The place had lots of bedding, it was warm and inviting, had everything we needed. My daughter thought the “balcony” on the second floor which over looked the kitchen was cool! "
United States
Soonae S.
The price is NZ$1,150
includes taxes & fees
21 Oct - 22 Oct
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

12. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is NZ$887
includes taxes & fees
4 Nov - 5 Nov
Pines Vignette • Modern 3BR Home in Windham
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

13. Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!

Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is NZ$801
includes taxes & fees
29 Oct - 30 Oct
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
A fire pit with two chairs in a backyard.

14. Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
The price is NZ$1,063
includes taxes & fees
4 Nov - 5 Nov
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
A covered outdoor area with a sofa, a table with a grill, and a tripod-mounted camera.

15. Gorgeous Mountains Views & Private Stream in Secluded Oasis

Gorgeous Mountains Views & Private Stream in Secluded Oasis
Gilboa
10.0 out of 10, Exceptional, (8 reviews)
"Our stay was great: attentive host, comfortable lodgings, beautiful setting."
United States
Carrie S.
The price is NZ$751
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountains Views & Private Stream in Secluded Oasis
Interior

16. Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street

Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street
West Kill
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful setting. Great light throughout the house. Convenient to the ski mountains"
United States
Timothy M.
The price is NZ$1,223
includes taxes & fees
13 Oct - 14 Oct
Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street
A spacious living area with a large window, a ceiling fan, and a dining table set for four.

17. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"Very clean and comfy place to stay. Communication with owner is quick and easy. Highly recommendations "
United States
ching yi t.
The price is NZ$1,333
includes taxes & fees
25 Oct - 26 Oct
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

18. Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15

Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15
West Kill
10.0 out of 10, Exceptional, (1 review)
"It was a great spot for all three generations to be together for the holiday. House was clean and close to lots of hikes. Hosts were available."
United States
Kate R.
The price is NZ$2,262
includes taxes & fees
12 Oct - 13 Oct
Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15
A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, and an oven. There is a wooden ceiling and a blue rug on the floor.

19. Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Hunter
9.6 out of 10, Exceptional, (13 reviews)
"Everything was great!"
United States
Samuel S.
The price is NZ$1,450
includes taxes & fees
25 Oct - 26 Oct
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
A dining area with a wooden table, a woven pendant light, candles, a bottle of wine, and a vase with flowers.

20. Hot Tub • Game Room • Fire Pit • 15 Private Acres

Hot Tub • Game Room • Fire Pit • 15 Private Acres
East Jewett
10.0 out of 10, Exceptional, (7 reviews)
"My family and I had a wonderful experience at this property. The house was clean, nicely decorated and had everything you need to feel at home! Jeff, the host , was so helpful and accommodating. We will definitely be back!"
United States
Beth C.
Hot Tub • Game Room • Fire Pit • 15 Private Acres
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"We absolutely loved our stay here. Sadly, we were only here for one night but it was the perfect pit stop for our roadtrip. The room was huge and the views are amazing. We arrived late and the staff was so helpful & recommended places that were still open to eat. Also so close to all the trails! We will be back and will stay here longer!"
Ember 1-night trip
Posted 20 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
247
Accommodation
553 Holiday Homes
Lowest Price
NZ$407
Highest Price
NZ$2,262